The Secret Life of a Bay Street Hooker

The X-rated trade secrets of a Bay Street call girl. She’s sophisticated, smart and open minded. She meets her clients at Le Germain or the Hazelton and gives them what they want. By Leah McLaren | Illustrations by Jack Dylan

On an unseasonably warm evening in October, Chloë Marcelle decided to walk to work. Her slim figure encased in a silk blouse, silver-speckled Chanel leather skirt, net stockings and black silk Manolos, she left her apartment and strolled through the downtown core to her favourite boutique hotel, Le Germain on Mercer Street.

One thing you should probably know about Chloë before you read any further is that “Chloë Marcelle” is not her real name. It’s an alias she uses, as all escorts do, for the purpose of separating her real life (single mom, graduate degree holder) from her sex trade persona (naughty little minx, does bareback blow jobs but no anal). Dark-haired, pretty and creamy-skinned, she could be Italian, French or Greek. She’s in her mid-30s but could easily pass for 29. She has a knockout body: medium height, trim, toned and teacup-breasted. Her teeth, which she reveals often in easy, winning smiles, were recently straightened and bleached. Her wide-open daisy eyes suggest a fondness for cosmetic filler. But more striking than any of this is her effervescence. She is witty, insightful and self-revealing by turns. In other words, good value for money.

In the minimalist cocktail lounge at Le Germain, she meets her client. Let’s call him Ed. Ed is a regular. A successful Toronto businessman in his mid-60s, he’s a widower with no interest in remarrying. Chloë has been seeing him for more than a year now. They meet a couple of times a month to catch up and enjoy each other’s company.

Ed is in a good mood, as usual. He greets her with a kiss on the cheek and a compliment on her appearance, which she happily accepts, having spent many hours primping, shaving and hot-rollering her hair into submission in anticipation of their date. They have cocktails—a martini for her and scotch for him—then take a taxi to Zucca Trattoria on Yonge Street. The restaurant is Chloë’s choice, recommended to her by a chef friend. Ed orders the four-course tasting menu for two and a bottle of her favourite pinot grigio. Over the meal they chat about work and family. Ed is curious about what Chloë does with her days. She mentions her devotion to yoga and Pilates and how she likes to sew. He thinks this is funny. “You’re retired,” he teases her, and they both have a good laugh. The joke, of course, is that she’s working as they speak. What she doesn’t mention is that she has two children, a boy and a girl under the age of 10, who are at home right now with her ex‑boyfriend (their father).

In addition to grooming and yoga, Chloë spends most days updating her Web site, communicating with clients, arranging her schedule and checking out the competition. Most Toronto independents, like Chloë, operate their own Web sites and advertise on such hubs as terb.ca (the Toronto Escort Review Board) and Eros Guide Toronto. She also reads the on-line review boards, where “hobbyists” (the industry term for men who use different call girls regularly, almost as a sport) congregate to rate and comment on different escorts. Her reviews are generally very good. One man calls her “the most wonderful and erotic experience of my life.” Another compares her to Miss Crump on The Andy Griffith Show and a young Suzanne Pleshette.

When Chloë isn’t ferrying her children around to after-school classes, she specializes in out-calls—meaning she will meet her clients at an agreed-upon location. Her work takes place almost entirely in high-end downtown hotels—the Hazelton, the King Eddie, the Park Hyatt—though she’s made calls to the Drake and the Gladstone, as well. She prefers Le Germain because the staff are unintrusive and the bar is dark and cozy. “A true gentleman’s hotel,” she calls it. She charges $375 an hour, $700 for two hours, and extra for travel outside the GTA. Most appointments last a couple of hours, but occasionally she gets booked on an overnight, for which she earns $2,600. Like this particular night.

Over dinner, Ed tells her about problems he’s having at the office—cutbacks and difficult decisions ahead. Chloë offers some sympathetic advice, then gently turns the conversation back to their date. With a coy smile, she begins painting a vivid picture of the lingerie hidden beneath her blouse and skirt.

They take a taxi back to the hotel and head up to Ed’s room. There is a thick envelope of cash on the dresser, and when Ed goes into the bathroom she slips it into her handbag. She doesn’t count it—she knows he’s good for the money. When Ed emerges, he presents Chloë with a token of his appreciation: an amber necklace and a pair of earrings. Nothing precious or pretentious, just a simple gift that’s suited to her understated style. Chloë is touched.

Instead of saying thank you, she kisses him. She always makes the first move. A deep, intimate French kiss. Like a teenage girl, she prides herself on make-out technique. It took her a while to realize that clients expect her to take control in this way, to be the professional who guides the action—which she does, all the way through to the end. Sex, pillow talk, massage and sleep.

At 6:45 a.m., she unlocks the front door to her apartment. She has 15 minutes to change before the kids are up.

Toronto has traditionally been an agency town—a hub city that attracts a high number of international (mostly American) business travellers, lonely, road-weary and willing to pay escort agencies for company. Hard numbers are difficult to come by, since most sex work is conducted under the table, but people who work in the industry say there are roughly 50 out-call agencies operating in Toronto. (Of these, 10 to 20 are considered established, professionally run and profitable high-end outfits.) Agency escorts have for years operated openly and with minimal police interference simply because it isn’t cost effective for police to go after them.

Terb.ca lists escort agencies as well as independent escorts, massage parlours (or “holistic healing centres,” as they are sometimes called) and independent masseuses. The larger, more established agencies, such as Cupid’s, Select and Mirage, have anywhere from 20 to 50 escorts working for them at a time. Smaller outfits, such as Exquisite or Aphrodite’s, have only a handful.

High-end escorts are, by and large, either full-time students or career women moonlighting for extra cash. Ranging in age from late teens to mid-30s (though with a mean age closer to mid-20s), most escorts are either Caucasian and Canadian born or of Asian or eastern European descent. When a woman is on call, she either waits at home or goes to the agency office space. Once a client calls for her, she’s then taken by car to a hotel or residence (though most agency work is done in hotel rooms) to meet them. The driver will wait for her outside. Higher end outfits in Toronto charge around $250 an hour, with the agency taking anywhere from 35 to 50 per cent. Escorts here are a bargain compared to New York, where many agencies charge between $600 and $1,500 an hour. (The most notorious is the Emperor’s Club, the agency that booked Eliot Spitzer’s infamous night with Ashley Dupré, which cost him $4,300 and his career.)

The agency market in Toronto is close to saturated. “We’ve got girls coming from Vancouver, Halifax and Montreal who all want to work in this city, and this has kept prices down,” says one of the more reputable agency owners. His company, one of the biggest in the country, employs roughly 50 escorts, three receptionists (“phone girls” in escort parlance) and six drivers, and operates out of a commercial office space downtown. He claims to clear only about $50,000 to $60,000 a year in profit. He also has a full-time job and a wife and family.

The glut of agencies in Toronto may help explain the rise in the number of independent escorts, as more and more women seek to carve out more money for themselves. That, along with the growth of the Internet and the fact that the laws governing prostitution have made it easier for the escort industry to operate safely and with relative impunity. While buying and selling sex isn’t technically illegal, federal laws introduced in 1985 made many of the activities surrounding it illegal. These included running a bawdy house, living off the avails of prostitution and, most importantly, communicating for the purpose of prostitution. The latter was an attempt to address the conspicuous nature of street prostitution, but it created what activists have called a “two-tier” sex trade, dividing prostitutes into those who work the streets (an estimated five to 20 per cent of prostitutes) and those who work indoors.

In September, Ontario superior court judge Susan Himel ruled that these three key provisions violated the Charter of Rights and contributed to the danger faced by prostitutes. The prohibition against bawdy houses made many sex workers dependent on strangers in vehicles; the inability to live off the avails of prostitution made it illegal for sex trade workers to organize as employers and employees and to take certain precautions, like hiring security guards; and the communication provision forced already vulnerable street prostitutes to make hasty and potentially dangerous decisions for fear of being prosecuted by police.

The decision will have little effect on the majority of escorts doing out-calls, which were, barring those provisions, already legal. However, it does open the door to more prostitutes doing in-calls, or working freely out of their homes. Alan Young, the criminal lawyer who led the court challenge, predicts the ruling will clear the path for even more high-end independents, whom he calls “the new generation” of Toronto sex workers. “The vast majority of sex work takes place indoors and is, by extension, lower risk,” he says.

Himel acknowledged that her decision could lead to a rise in brothels—although from most accounts, that particular horse has already left the barn. Valerie Scott, a sex trade worker and one of the applicants in the case, has said that she finds the fear of brothels on every street laughable. “Every block in Toronto already has a brothel on it. People just don’t know it.”

“I’d say that most condos in this city have escorts working out of them,” says Detective Wendy Leaver of the Toronto Police Service Special Victims Unit

Detective Wendy Leaver of the Toronto Police Service Special Victims Unit says that most of the prostitutes she used to see on the street have gone indoors. “Besides the escort agencies, you have the women in the massage parlours and those working inside the condos and apartments,” she says. “Very few condos in the city would not have escorts working out of them.” She confirms that there are already at least 200 in-call agencies, or brothels, operating in the city.

Both the federal and provincial governments have already launched appeals to Judge Himel’s ruling, but if it stands, Toronto sex trade workers would be free to operate out of their homes, hire a secretary, bodyguard and driver, all without fear of police interference. They could conduct their business openly and professionally, declaring their occupations on their tax returns and lobbying for industry standards and health regulations. The ruling has been hailed by the city’s sex trade activists as a victory in helping to ensure the safety of prostitutes everywhere. It may also help do away with some of the trade’s attendant paranoia. As one independent escort recently confided to me, “Everything within the law was so grey. If I met a client more than once in his home, it would be classed as a bawdy house. If I did in-calls, it would be the same.” She says she knows and trusts her clients and would feel that much more secure if she could use her own place. “I know what I do isn’t criminal,” she says. “But every time I see a cop, I think they’re looking for me.”

On the face of it, there is nothing exceptional about Chloë’s upbringing. She grew up in north Toronto in what she describes as a “close-knit and traditional” middle-class family. Chloë recalls a sheltered childhood influenced by religion. She won’t reveal which faith. Her exact age, real name and religious background are the only three topics she refuses to discuss.

According to Chloë, she was only 11 when her father died, though she insists the event did not scar her. “He was an authoritarian,” she says. “I shed a few tears, and I was freed.” While some of her family members turned inward, Chloë became a rebellious teen. She got kicked out of high school for truancy and enrolled in a cosmetology course at a community college. Though she acted out, it was not with boys. Chloë didn’t lose her virginity until she was 18.

Eventually, she decided to go back to school and enrolled in the undergrad program at York, where she majored in history. (She would later complete a master’s degree in the same subject.) Her favourite historical figure was Louis XIV. She loved the stories of life at court in Versailles—the opulence, the decadence, the shameless promiscuity. “I remember reading about the lives of his mistresses and thinking, ‘That’s the life.’ ”

Her transformation into “Chloë” did not occur in a seedy nightclub or dark back alley. There were no pimps or oily strip club managers involved in her evolution from good girl to what she calls “the H word” (hooker). Instead, it occurred in a thoughtful, austere sort of way: in a lecture hall at York. It was there that she first encountered the works of Michel Foucault. Reading him, she remembers, she felt something blooming inside her. The French postmodernist articulated everything she had suspected about the world but hadn’t yet found the words to express. She began openly questioning accepted notions of sexuality and gender and dismissing morality as a vague social construct. She found herself wondering things like, Why can’t I work with my vagina when other people work with their hands? And what’s the point of breaking from religion if you don’t break from religious cultural taboos, as well?

Soon after, Chloë began putting ads on the “Intimate Encounters” sections of such dating sites as Lavalife and Ashley Madison—the sections where people look for hookups as opposed to relationships. The proposition was clear: she was an attractive young woman willing to provide company and sex in exchange for gifts. Some men took her shopping for clothes. Another bought her groceries. No money changed hands. While the dates served as a way for Chloë to dip a pedicured toe into the shallows of sex work, she soon realized that a girl cannot live on Holt Renfrew gift cards alone. “It took me a long time to get to the point where I could admit what it was I was after,” she says.

Around the same time, she became involved in a relationship with a male neighbour, a fellow student. Though she says she never envisioned herself spending the rest of her life with him—they never married or even officially cohabited during their eight years together—they both wanted children. She got pregnant toward the end of her undergrad degree and had her son; three years later, during her first masters degree, she had her daughter.

While working on her second graduate degree—this one in education—Chloë decided to officially make the leap into professional escorting. She claims that everything in her life pointed toward it. “When I tried to look for a straight job, sexuality kept coming up in the interviews. I never knew if the managers were serious or if they wanted to take things further and discuss it over a drink. At a certain point, I just felt it was my calling.” She worked briefly as a supply teacher but didn’t like it.

Her ex is a dedicated co-parent. While she provides sole financial support for the children, he provides child care on a moment’s notice. He is one of a tiny circle of friends who know what she does for a living. He doesn’t like it, she says, but he also knows he doesn’t have a say.

When Chloë first decided to go pro, she signed up at an agency specializing in high-end escorts for hour-long sessions, courtesan dinner dates or business travel. She worked hard, sometimes doing as many as five or six calls a night. She was popular with clients, who often made repeat appointments. For the most part, Chloë says she enjoyed the work. The manager who ran the place was good to her and helped show her the ropes. But agency escorts can’t be as choosey about their clients as independents. “The ick factor is much higher,” she says.

Many clients keep in touch on a daily basis, sending affectionate texts and e-mails. “They really do think of me as their girlfriend, and I see them as the men I’m dating”

There were the cheap guys, who tried to trick her into staying longer than they were paying for. And there were the hobbyists, who would book three or four agency girls back to back. There was also a rich crackhead who liked to order her up when he was on a binge. Sometimes they’d hang out in a room at the Four Seasons, or at his luxuriously appointed midtown penthouse. “Sometimes he was so high he couldn’t even have sex,” she remembers. “The smell of crack permeated his skin. He smoked constantly. The pipe never left his hand.”

Chloë worked for the agency on and off for a couple of years, to pay her way through grad school. “In the end, the work came to feel like a bit of a grind,” she says, adding with a grin, “no pun intended.” She also had nagging concerns about safety. While agencies provide a buffer between the client and the prostitute, they also reduce her ability to make decisions for herself. The women on the front desk don’t necessarily have the interests of the escort in mind, and are liable to be less discerning about, say, a prospective client who communicates in an aggressive manner. “People think if you work at an agency you’re more protected, and that’s just not true,” Chloë explains. “There’s no big burly guy to step in and defend you. Agencies aren’t into protecting girls; they’re into making money.”

Since going independent two years ago, Chloë has been making between $70,000 and $90,000 a year, in cash. She has a sizable amount of money (in the low six figures) squirrelled away in safety deposit boxes around the city. “I make sure to save about 30 per cent of my income,” she says. “I have goals for my children, and I want to buy a house at some point.” She says she aims to earn between $5,000 and $8,000 a month and can usually do so by working two or three nights per week on average. “It fluctuates wildly. I can’t control the market or men’s libidos.” Some months are better than others. For example, summers are notoriously dismal because clients go on family holidays. For Chloë, last summer’s dry spell ended when a Saudi Prince flew into town and hired her for an overnight.

Chloë pays her taxes on time every year. On her tax return, she claims to be a freelance writer. Her expenses—lingerie, makeup, clothing, electrolysis—are relatively low. She is teaching herself how to do her own Web design and recently had business cards made. Next time you find yourself in the bar or lobby of the Hazelton or Four Seasons, keep an eye out for them. They depict a young woman, face obscured, lithe body in a leopard print cami with garters and stockings. On the back is her Web address.

As an independent, Chloë does better with older men than young ones. For one thing, they can afford her. For another, they are more interested in the art of conversation, one of her more mentionable talents. Today, her regular client base consists largely of executive types (Bay Street lawyers and bankers predominate) ranging in age from 40 to late 60s, with wives and children safely ensconced in houses on leafy streets uptown.

For these married men, Chloë offers a service that, in on-line sex trade parlance, is known as the GFE or “the girlfriend experience.” This means that in addition to sex, she provides conversation, companionship, kissing and cuddling—a deeper and more comprehensive intimate experience, not unlike an old-fashioned courtesan. Some clients like to take her out for dinner first. Others prefer a morning appointment followed by lunch. One regular, an engineer, often books theatre tickets. Another sometimes takes her out to lunch during the week just to catch up (for this, she doesn’t charge). Occasionally, if a client is single, he will even take her as his date to a wedding or a work event. If anyone asks how they met, she responds truthfully: “On the Internet.”

Many keep in touch with her on a daily basis, sending affectionate texts and e-mails and sharing the details of their lives, just as they would in a normal relationship. “They really do think of me as their girlfriend,” Chloë says. “And I see them as the men I’m dating.” She gives and receives unprotected oral sex but uses a condom for intercourse. She gets tested regularly for STDs.

Summers are notoriously dismal because clients go on family holidays. For Chloë, last summer’s dry spell ended when a Saudi prince flew into town and hired her for an overnight

Call girls offering GFE stand in sharp contrast to those specializing in PSE—porn star experience—which generally means hardcore sex with little romantic or social inter­action involved. The problem with the GFE is that it can lead to emotional complications. One client, a married man who works in the software business, recently sussed out her real identity through exhaustive on-line searching. Once he’d figured out her name and address, he sent flowers to her home. Chloë was not amused. She is protective of her real-life identity and is not on Facebook or Twitter for precisely that reason. At their next meeting, she warned the client he needed to respect her boundaries, but she didn’t stop seeing him.

For Chloë, working and living in the downtown core means her two lives occasionally intersect. Once she bumped into a regular client while he was shopping for produce with his wife in Kensington Market. The wife, she remembers, was attractive and elegant. “You should have seen the look on his face; I thought he was going to die!” Another client turned out to be the brother of a friend. They’d never met, but she recognized him right away. When she explained the connection, the client was fine with it. Sometimes she takes her daughter for a play date across the street from a former client’s house in Little Italy. “I keep expecting him to appear on his front step, but thank God he never has,” she says.

According to Chloë, none of her married clients are interested in leaving their wives. If anything, she says, they are protective of their marriages, preferring a clear-cut arrangement with a hooker to the risk and drama of a full-blown extra-marital affair. “It’s a myth that men talk about their marital problems with escorts,” she says. “If they do talk about their marriages, it’s generally to say that they aren’t having sex at home.” Even if they are, it may not be the kind of sex they’re after. There are some things most men want, she explains, but aren’t comfortable asking of their partners. Asked to elaborate, she looks coy, then lowers her voice and tells me that she does “a lot of anal work” with her clients. This is an erogenous zone most women overlook in men, she says: “I have a little strap-on I sometimes like to put on, and they’re totally into it. I’ve only ever had one client turn me down.”

Like most independents, Chloë has a strict set of standards a new client must meet—a security checklist of sorts—before she will confirm a booking. Part of this checklist is to minimize the risk of dangerous clients, but mostly it’s just to weed out the tire kickers. For an independent escort, time wasters are the biggest liability—the teenagers pulling pranks, the cheapskates who want explicit photos or men who simply want to e-mail back and forth for hours. There are the guys who don’t have the nerve to meet in person but just get off on the idea of a prostitute. She estimates that half the people who contact her are not serious about going through with a booking. “It’s like nicky nicky nine doors,” she says. “And if you’re not careful, it can eat up all your time.”

New clients must provide either a real name and work phone number or two references from other respected call girls. Alternatively, she’ll accept a $100 deposit via e-mail money transfer. She, in turn, is regularly asked to provide references for her own clients. Independent escorts keep track of who’s working in the industry through the Internet review boards and hub sites.

It’s not a foolproof system. Just recently she lost a night’s work with a visiting American businessman who’d booked her to come to a hotel near the airport. He gave her a room number, but when she called and asked the front desk to check the booking, they gave her a woman’s name. She got a bad feeling and opted to stay home with her kids. It wasn’t until later that the client got in touch to say the room was booked under his secretary’s name. For a call girl, that’s just the cost of doing business. (He did book her the next time he came through town.)

For Chloë, sex is the easy part. It’s the secrecy that’s hard. Last year, when her daughter had a “What my mommy does for work” project for school, Chloë said she was a freelance copywriter for an ad firm (a job she’d tried briefly in the past). “It’s going to be more difficult to fool them as they get older,” she says, “and they notice most of my work takes place after 11 o’clock at night and that I wear high heels and cocktail dresses to work.”

Since breaking up with her ex, Chloë has dated a couple of men but has never allowed things to get serious. Nor has she ever been open about her profession with anyone she was romantically involved with (apart from her ex). She feels her profession is best conducted without the inter­ference of a jealous partner, and she wouldn’t want to be put in the position of having to choose between her profes­sion and her relationship. As a result, in the past two years she’s only had sex once without being paid for it.

Like a dancer or a model, a high-end call girl’s career arc is relatively short, the big earning years cut off by the merciless market demand for youth. A couple of times during our interviews, she says she’d like to marry one of her clients, a divorced businessman who is fond of her but unfortunately doesn’t “do” kids. Another time, she mentions she’s considered finding work in sales or marketing.

The last time we meet for lunch she arrives breathless, buoyant and 10 minutes late. A young businessman in his 20s just tried to pick her up in the street. When he suggested a drink, she smiled and said it sounded like he needed to get laid. The man staggered back, then looked interested, so she handed him a business card and walked away. He hasn’t called yet, but she’s certain he will.